SN1-type reactions in the presence of water: Indium(III)-promoted highly enantioselective organocatalytic propargylation of aldehydes

Sinisi R.; Vita M.V.; Gualandi A.; Emer E.; Cozzi P.G.

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SN1-type reactions in the presence of water: Indium(III)-promoted highly enantioselective organocatalytic propargylation of aldehydes

机译：在水存在下的SN1型反应：铟（III）促进的醛的高对映选择性有机催化炔丙基化

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Water under troubled chemistry! The first catalytic stereoselective addition of aldehydes to internal functionalized propargylic alcohols promoted by a combination of organocatalysis and indium triflate is described (see scheme). The reaction is tolerant of functional groups (FG) and was performed in the presence of water. High enantioselectivities (anti, 92-99 % ee) and moderate diastereomeric ratios (d.r., up to 6.7:1 for the anti isomer) were obtained.

机译：化学物质中的水！描述了通过有机催化和三氟甲磺酸铟的组合而促进的向内部官能化的炔丙醇中的醛的第一次催化立体选择性加成（参见方案）。该反应对官能团（FG）具有耐受性，并且在水的存在下进行。获得了高对映选择性（抗92-99％ee）和适度的非对映异构体比率（抗异构体的d.r.高达6.7：1）。

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《Chemistry: A European journal》 |2011年第27期|共5页
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Sinisi R.; Vita M.V.; Gualandi A.; Emer E.; Cozzi P.G.;
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正文语种 eng
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aldehydes; enamine; indium; organocatalysis; propargylation;

机译：醛;烯胺;铟;有机催化;炔丙基化;

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1. SN1-type reactions in the presence of water: Indium(III)-promoted highly enantioselective organocatalytic propargylation of aldehydes [J] . Sinisi R., Vita M.V., Gualandi A., Chemistry: A European journal . 2011,第27期

机译：在水存在下的SN1型反应：铟（III）促进的醛的高对映选择性有机催化炔丙基化
2. One-step, efficient synthesis of combined threonine-surfactant organocatalysts for the highly enantioselective direct aldol reactions of cyclic ketones with aromatic aldehydes in the presence of water [J] . Wu C., Fu X., Ma X., Tetrahedron, Asymmetry: The International Journal for Repid Publication on all Aspects of Asymmetry in Orgainc, Inorganic, Organometallic, Physical and Bio-Organic Chemistry . 2010,第20期

机译：一步法高效合成苏氨酸表面活性剂有机催化剂，用于在水存在下环状酮与芳族醛的高度对映选择性直接羟醛反应
3. Highly diastereo- and enantioselective direct aldol reactions of aldehydes and ketones catalyzed by siloxyproline in the presence of water [J] . Aratake S, Itoh T, Okano T, Chemistry: A European journal . 2007,第36期

机译：甲硅烷氧基脯氨酸在水的存在下对醛和酮的高度非对映和对映选择性直接羟醛反应
4. Enantioselective Organocatalytic Michael Addition of Aldehydes to β-Nitrostyrenes [C] . Marju Laars, Kerti Ausmees, Tonis Kanger European Symposium on Organic Chemistry . 2009

机译：对β-硝化丁烯的映选择性有机催化迈克尔添加醛
5. Part I. Asymmetric organocatalysis: (1) Direct enantioselective organocatalytic hydroxymethylation of aldehydes catalyzed by alpha,alpha-diphenylprolinol trimethylsilyl ether: Application in the formal synthesis of (-)-Rasfonin; (2) Synthesis of a novel bicyclic secondary amine organocatalyst: Application to the direct enantioselective organocatalytic hydroxymethylation of aldehydes. Part II. Asymmetric synthesis of bicyclic analogues of the anti-osteoporotic drug risedronate. [D] . Miller, John Robert. 2010

机译：第一部分，不对称有机催化：（1）α，α-二苯基脯氨醇三甲基甲硅烷基醚催化的醛的直接对映选择性有机催化羟甲基化：在（-）-Rasfonin的正式合成中的应用；（2）新型双环仲胺有机催化剂的合成：应用于醛的直接对映选择性有机催化羟甲基化。第二部分抗骨质疏松药物Risedronate的双环类似物的不对称合成。
6. Organocatalytic cascade aza-Michael/hemiacetal reaction between disubstituted hydrazines and αβ-unsaturated aldehydes: Highly diastereo- and enantioselective synthesis of pyrazolidine derivatives [O] . Zhi-Cong Geng, Jian Chen, Ning Li, 2012

机译：双取代肼与αβ-不饱和醛之间的有机催化级联氮杂-迈克尔/半缩醛反应：吡唑烷衍生物的高度非对映和对映选择性合成
7. Organocatalytic cascade aza-Michael/hemiacetal reaction between disubstituted hydrazines and α,β-unsaturated aldehydes: Highly diastereo- and enantioselective synthesis of pyrazolidine derivatives [O] . Zhi-Cong Geng, Jian Chen, Ning Li, 2012

机译：二取代肼与＆＃945;＆＃946; - 不饱和醛之间的有机催化级联氮杂 - 迈克尔/半缩醛反应：高度非对映体和对映选择性合成吡唑烷衍生物

SN1-type reactions in the presence of water: Indium(III)-promoted highly enantioselective organocatalytic propargylation of aldehydes

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